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Synthesis of a novel universal opioid receptor agonist with the 1,3,5-trioxazatriquinane skeleton and its pharmacologies.

Abstract：

:We designed and synthesized of 1,3,5-trioxazatriquinanes with o- or p-hydroxyphenyl rings as analogs of the κ opioid receptor agonist SYK-146 with m-hydroxyphenyl groups. Although almost all tested compounds did not bind to the opioid receptors, only 17b (SYK-524) with two o-hydroxyphenyl rings showed moderate or potent binding affinities and exhibited agonistic activities for the three opioid receptor types. Because the basicity of the nitrogen atom in the 1,3,5-trioxazatriquinane structure was predicted to be very low due to the electron withdrawing effect of the three oxygen atoms, SYK-524 was a novel non-morphinan and nonpeptidic opioid universal agonist lacking a basic nitrogen atom.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Hirayama S,Wada N,Kuroda N,Iwai T,Yamaotsu N,Hirono S,Fujii H,Nagase H

doi

10.1016/j.bmcl.2014.08.012

subject

Has Abstract

pub_date

2014-10-15 00:00:00

pages

4895-8

issue

20

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(14)00843-9

journal_volume

24

pub_type

杂志文章

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